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Which of the following is expected to ge...

Which of the following is expected to generate more stable carbocation on the heterolysis of C-I bond?
`CH_(3)-O-CH_(2)-1, CH_(3)-overset(H)overset(|)(N)-CH_(2)-1`

Text Solution

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In the first case the carbocation generated is stablized by resonance due to the lone pair of O The same happens in the second case, but now due to the lone pari of . N being less electrogenative can provide electrons easily Hence (ii) is expected to generate more stable carbocation
`CH_(3)-NH-CH_(2)-1rarr[CH_(2)-overset(H)overset(|)(N)-overset(o+)(CH_(2))harrCH_(3)-underset(H)underset(|)overset(o+)(N)=CH_(2)]`
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